1245706-89-1

Upstream product

• 100-42-5 styrene 
• 5656-71-3 2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 1437786-66-7 2-(2-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 536-74-3 phenylacetylene 
• 1214264-88-6 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 300-57-2 allylbenzene 
• 479-27-6 naphthalene-1,8-diamine 

Relevant academic research and scientific papers

Mixed diboration of alkenes in a metal-free context

Experimental and theoretical rationalization on regioselective mixed diboration of alkenes, with the unsymmetrical diboron reagent Bpin-Bdan, providing the protecting Bdan moiety in the internal position.

Synthesis of stereodefined 1,1-diborylalkenes via copper-catalyzed diboration of terminal alkynes

A copper-catalyzed method for the E-selective 1,1-diboration of terminal alkynes is described. The tandem process involves sequential dehydrogenative borylation of the alkyne substrate with HBdan (1,8-diaminonaphthalatoborane), followed by hydroboration w

A cysteamine-selective two-photon fluorescent probe for ratiometric bioimaging

We report a two-photon fluorescent probe for ratiometric imaging of cysteamine in situ. This probe can detect the levels of endogenous cysteamine with statistical significance in live cells and brain hippocampal tissues, revealing that cysteamine is localized mainly in the perikaria of the pyramidal neurons and the granule cells.

Copper-Photocatalyzed Hydroboration of Alkynes and Alkenes

The photocatalytic hydroboration of alkenes and alkynes is reported. The use of newly-designed copper photocatalysts with B2Pin2 permits the formation a boryl radical, which is used for hydroboration of a large panel of alkenes and a

NHC-copper-thiophene-2-carboxylate complex for the hydroboration of terminal alkynes

An air-stable N-heterocyclic carbene-copper thiophene-2-carboxylate (CuTC) complex has been prepared for the stereoselective hydroboration of terminal alkynes using pinacolborane (HBpin) or 1,8-naphthalenediaminatoborane (HBdan). The newly synthesized complex can be directly activated by hydroboranes without a cocatalyst such as a base, and exhibits high reactivity for the hydroboration of alkynes under mild conditions. A gram-scale hydroboration of terminal phenylacetylene demonstrated the applicability of the copper complex for the preparation of alkenyl boronates.

Alkynylboranes: A practical approach by zinc-catalyzed dehydrogenative coupling of terminal alkynes with 1,8-naphthalenediaminatoborane

Under zinc Lewis acid catalysis, terminal alkynes coupled dehydrogenatively with 1,8-naphthalenediaminatoborane [HB(dan)]. It is important to note that the resulting alkynylboranes with an C(sp) - B(dan) bond are isolable by column chromatography on silica gel (SiO2) and are usable as coupling partners for palladium- and copper-catalyzed cross-coupling reactions with (hetero)aryl halides.

Regio- and enantioselective copper(I)-catalyzed hydroboration of borylalkenes: Asymmetric synthesis of 1,1-diborylalkanes

A bisphosphine/copper catalyst was used for the asymmetric hydroboration of 1,8-naphthalenediaminatoboryl (Bdan) substituted alkenes (see scheme; pin=pinacolato). Simple alkyl-substituted borylalkenes and styrene derivatives were hydroborated with high regio- and enantioselectivity. The electronic and steric properties of the Bdan group significantly affected the reactivity and regioselectivity of hydroboration.

Rhodium-catalyzed dehydroborylation of styrenes with Naphthalene-1,8- diaminatoborane [(dan)BH]: New synthesis of masked β-borylstyrenes as new phenylene-vinylene cross-coupling modules

Styrene derivatives underwent dehydroborylation with naphthalene-1,8- diaminatoborane [(dan)BH] in the presence of a cationic rhodium complex, giving β-borylstyrene derivatives in good yields. Thus prepared β-borylstyrenes bearing a chlorine or B(pin) group on their aromatic rings were utilized for the synthesis of highly conjugated molecules through stepwise cross-coupling, taking advantage of the dan group as an effective protective group for a boronyl group.